1,2,3,4-tetrafluoropentacene-6,13-dione | 859849-45-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 并五苯醌
• 英文名称: 1,2,3,4-tetrafluoropentacene-6,13-dione
• 英文别名: 1,2,3,4-Tetrafluoropentacene-6,13-dione
• CAS: 859849-45-9
• 化学式: C₂₂H₈F₄O₂
• 分子量: 380.298
• InChiKey: SPXVRUORZUUVEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrafluoropentacene-6,13-dione 、 三异丙基硅基乙炔 在 正丁基锂 作用下， 以 正己烷 、 四氢呋喃 为溶剂， 反应 12.5h， 生成 1,2,3,4-Tetrafluoro-6,13-bis-[(triisopropylsilanyl)-ethynyl]-6,13-dihydro-pentacene-6,13-diol
  参考文献：
  名称：

  Synthesis and Characterization of Electron-Deficient Pentacenes

  摘要：

  Halogen functional groups on pentacene can be used both as synthetic handles for further functionalization as well as to tune the pi-stacking in these systems. The halogenated pentacene derivatives described here (X = Br, X' = H, and X = X' = F) are all stable and soluble, with reduction potentials significantly lower than that of the parent functionalized pentacene (X = X' = H). The bromopentacenes could be further elucidated to pentacene nitriles, further decreasing the acene's reduction potential, while the charge-carrier mobility in the fluorinated systems was shown to scale with the degree of fluorine substitution.

  DOI：

  10.1021/ol050872b
• 作为产物：
  描述：

  3,4,5,6-四氟-1,2-苯二甲醇 在 氢溴酸 、 potassium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 1,2,3,4-tetrafluoropentacene-6,13-dione
  参考文献：
  名称：

  Synthesis and Characterization of Electron-Deficient Pentacenes

  摘要：

  Halogen functional groups on pentacene can be used both as synthetic handles for further functionalization as well as to tune the pi-stacking in these systems. The halogenated pentacene derivatives described here (X = Br, X' = H, and X = X' = F) are all stable and soluble, with reduction potentials significantly lower than that of the parent functionalized pentacene (X = X' = H). The bromopentacenes could be further elucidated to pentacene nitriles, further decreasing the acene's reduction potential, while the charge-carrier mobility in the fluorinated systems was shown to scale with the degree of fluorine substitution.

  DOI：

  10.1021/ol050872b

文献信息

• Synthesis and Characterization of Electron-Deficient Pentacenes
  作者：Christopher R. Swartz、Sean R. Parkin、Joseph E. Bullock、John E. Anthony、Alex C. Mayer、George G. Malliaras

  DOI：10.1021/ol050872b

  日期：2005.7.1

  Halogen functional groups on pentacene can be used both as synthetic handles for further functionalization as well as to tune the pi-stacking in these systems. The halogenated pentacene derivatives described here (X = Br, X' = H, and X = X' = F) are all stable and soluble, with reduction potentials significantly lower than that of the parent functionalized pentacene (X = X' = H). The bromopentacenes could be further elucidated to pentacene nitriles, further decreasing the acene's reduction potential, while the charge-carrier mobility in the fluorinated systems was shown to scale with the degree of fluorine substitution.